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Compounds and therapeutical uses thereof

a technology of compounds and active ingredients, applied in the field of medicinal chemistry, can solve the problems of bone marrow toxicity, cancer cells losing the capacity to undergo cell suicide, and toxicity of cells

Inactive Publication Date: 2013-01-31
MYREXIS INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patent is about a new discovery of compounds that can inhibit the growth of cancer cells by targeting a protein called tubulin and a protein called topoisomerase. These compounds can also activate a protein called caspase, which promotes cell death. This invention is important because it provides new potential treatments for diseases that are caused by the growth of cancer cells.

Problems solved by technology

This makes the cancer cells lose their capacity to undergo cellular suicide and the cells become cancerous.
Thus, a drug like 6-mercaptopurine can cause bone marrow toxicity while remaining ineffective for a slow growing tumor.
It was reported that substitutions on the phenyl ring resulted in reduced activity.

Method used

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  • Compounds and therapeutical uses thereof
  • Compounds and therapeutical uses thereof
  • Compounds and therapeutical uses thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

[1233]

(2-Chloro-quinazolin-4-yl)-(4-methoxy-phenyl)-methyl-amine

[1234]a) 2,4-Dichloroquinazoline: A suspension of 2,4-quinazolinedione (5.0 g, 30.8 mmol) in neat phosphorylchloride (50 mL) was heated under reflux for 18 h. The reaction mixture was concentrated under vacuum. The crude product was purified by chromatography (Silica gel) using ethyl acetate and hexane (1:4) to give 2,4-dichloroquinazoline as white solid (4.8 g, 96%). 1H NMR (CDCl3): 8.29 (ddd, J=8.4, 2.1 and 0.9 Hz, 1H), 8.04-8.00 (m, 2H), 7.75 (ddd, J=8.1, 4.8 and 3.0 Hz, 1H).

[1235]b) (2-Chloro-quinazolin-4-yl)-(4-methoxy-phenyl)-methyl-amine: A solution of 2,4-dichloroquinazoline (300 mg, 1.51 mmol) and 4-methoxy-N-methylaniline (248 mg, 1.81 mmol) in 5 ml isopropanol with a drop of concentrated HCl was stirred at room temperature for 8 h. White precipitates were observed in the reaction mixture. The reaction was filtered, and the solid was washed with isopropanol, and dried under vacuum to give white powder (260 mg,...

example 2

[1236]

(2-Chloro-quinazolin-4-yl)-(4-methyl-phenyl)-methyl-amine

[1237]The title compound was prepared from 2,4-dichloroquinazoline (250 mg, 1.25 mmol) and 4-methyl-N-methylaniline (196 mg, 1.43 mmol) by a procedure similar to Example 1b and was isolated as white powder (210 mg, 84%). 1H NMR (CDCl3): 8.69 (d, J=8.4 Hz, 1H), 7.75 (dd, J=8.1 and 7.5 Hz, 1H), 7.39 (d, J=7.8 Hz, 2H), 7.25 (d, J=7.8 Hz, 2H), 7.13 (d, J=8.2 Hz, 1H), 6.74 (d, J=8.7 Hz, 1H), 3.81 (s, 3H), 2.49 (s, 3H).

example 3

[1238]

(2-Chloro-quinazolin-4-yl)-(4-chloro-phenyl)-methyl-amine

[1239]The title compound was prepared from 2,4-dichloroquinazoline (60 mg, 0.302 mmol) and 4-chloro-N-methylaniline (50 mg, 0.332 mmol) by a procedure similar to Example 1b and was isolated as white powder (30 mg, 50%). 1H NMR (CDCl3): 8.66 (d, J=8.4 Hz, 1H), 7.78 (ddd, J=8.1, 7.5 and 2.4 Hz, 1H), 7.57 (d, J=8.7 Hz, 2H), 7.28 (d, J=8.7 Hz, 2H), 7.19 (ddd, J=8.1, 7.5 and 2.4 Hz, 1H), 6.79 (d, J=8.4 Hz, 1H), 3.83 (s, 3H).

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Abstract

Disclosed are 4-arylamino-quinazolines and analogs thereof that are effective as activators of caspases and inducers of apoptosis. The compounds of this invention are useful in the treatment of a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS[0001]This application is a divisional of prior U.S. application Ser. No. 12 / 500,863, filed Jul. 10, 2009, which is a continuation-in-part of prior U.S. application Ser. No. 10 / 885,903, filed Jul. 6, 2004; U.S. application Ser. No. 12 / 500,863 claims the benefit of U.S. Provisional Application No. 61 / 079,889, filed Jul. 11, 2008; and U.S. application Ser. No. 10 / 885,903 claims the benefit of U.S. Provisional Application No. 60 / 484,325, filed Jul. 3, 2003, U.S. Provisional Application No. 60 / 493,006, filed Aug. 7, 2003, U.S. Provisional Application No. 60 / 557,556, filed Mar. 29, 2004, and U.S. Provisional Application No. 60 / 571,288, filed May 14, 2004; the contents of all of which are hereby incorporated by reference herein in their entirety.FIELD OF THE INVENTION[0002]This invention is in the field of medicinal chemistry. In particular, the invention relates to compounds that are activators of caspases and inducers of apoptosis. The invention al...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): A61K31/517C07D403/04C07D413/12A61K31/5377C07D239/95C07D413/04C07D401/12C07D473/40A61K31/52C07D405/12A61K31/655C07D403/12A61K31/519C07D495/04C07D239/70C07D215/44A61K31/4706A61P35/00C07D239/94
CPCC07D239/94C07D239/95C07D401/12C07D487/04C07D403/12C07D405/12C07D403/04A61P35/00
Inventor ANDERSON, MARK B.WILLARDSEN, J. ADAMWEINER, WARREN S.YUNGAI, ASHANTAIHALTER, ROBERT J.KLIMOVA, YEVGENIYAKAZUYUKI, SUZUKIREEDER, MATTHEW
Owner MYREXIS INC
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